In Windows Server 2003 you could have multiple Remote Desktop session with the same user. In Windows Server 2008 this is not possible by default. If you login with the same user account the first session will be taken over by second session.

But you can allow multiple Remote Desktop sessions per user by changing a registry key.

Start regedit

Check out the follwoing registry keyHKEY_LOCAL_MACHINE\System\CurrentControlSet\Control\TerminalServer

If the fSingleSessionPerUser value doesn’t exist, create a new DWORD value named fSingleSessionPerUser

Open the fSingleSessionPerUser value. The possible values for this setting are as follows:0x0 Allow multiple sessions per user0x1 Force each user to a single session

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My name is Thomas Maurer. I am a Senior Cloud Advocate at Microsoft. I am part of the Azure engineering team and engage with the community and customers around the world. I am located in Switzerland. I am focusing on Microsoft technologies, especially cloud and datacenter solutions based on Microsoft Azure, Azure Stack and Windows Server. Opinions are my own.